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Electrochemical Intramolecular Aminooxygenation of Unactivated Alkenes
Author(s) -
Xu Fan,
Zhu Lin,
Zhu Shaobin,
Yan Xiaomei,
Xu HaiChao
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201404078
Subject(s) - intramolecular force , chemistry , electrochemistry , radical , selectivity , combinatorial chemistry , organic chemistry , photochemistry , catalysis , electrode
An electrochemical approach to the intramolecular aminooxygenation of unactivated alkenes has been developed. This process is based on the addition of nitrogen‐centered radicals, generated through electrochemical oxidation, to alkenes followed by trapping of the cyclized radical intermediate with 2,2,6,6‐tetramethylpiperidine‐ N ‐oxyl radical (TEMPO). Difunctionalization of a variety of alkenes with easily available carbamates/amides and TEMPO affords aminooxygenation products in high yields and with excellent trans selectivity for cyclic systems (d.r. up to>20:1). The approach provides a much‐needed complementary route to existing cis ‐selective methods.